Sequestration of Trace Metals Using Water-Soluble and Fluorous Phase-Soluble Polymers

Bergbreiter, David E.; Koshti, Nirmal; Franchina, Justine G.; Frels, Jonathon D.

doi:10.1002/(sici)1521-3773(20000317)39:6<1039::aid-anie1039>3.0.co;2-4

Cited by 48 publications

(48 citation statements)

References 14 publications

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“…[60] The realization of this idea in the synthesis of substituted ethyl cinnamates and cinnamic nitriles was recently reported. [137] Scheme 20. [133] A sulfoxide with a short fluorous tag was employed in Swern oxidations.…”

Section: Perfluoro-tagged Reagentsmentioning

confidence: 99%

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Tzschucke

Märkert

Bannwarth

et al. 2002

Angew. Chem. Int. Ed.

339

133

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The shift of paradigm in combinatorial chemistry, from large compound libraries (of mixtures) on a small scale towards defined compound libraries where each compound is prepared in an individual well, has stimulated the search for alternative separation approaches. The key to a rapid and efficient synthesis is not only the parallel arrangement of reactions, but simple work-up procedures so as to circumvent time-consuming and laborious purification steps. During the initial development stages of combinatorial synthesis it was believed that rational synthesis of individual compounds could only be achieved by solid-phase strategies. However, there are a number of problems in solid-phase chemistry: most notably there is the need for a suitable linker unit, the limitation of the reaction conditions to certain solvents and reagents, and the heterogeneous reaction conditions. Further disadvantages are: the moderate loading capacities of the polymeric support and the limited stability of the solid support. In the last few years several new separation techniques have been developed. Depending on the chemical problem or the class of compounds to be prepared, one can choose from a whole array of different approaches. Most of these modern separation approaches rely on solution-phase chemistry, even though some of them use solid-phase resins as tools (for example, as scavengers). Several of these separation techniques are based on liquid-liquid phase separation, including ionic liquids, fluorous phases, and supercritical solvents. Besides being benign with respect to their environmental aspects, they also show a number of advantages with respect to the work-up procedures of organic reactions as well as simplicity in the isolation of products. Another set of separation strategies involves polymeric supports (for example, as scavengers or for cyclative cleavage), either as solid phases or as soluble polymeric supports. In contrast to solid-phase resins, soluble polymeric supports allow reactions to be performed under homogeneous conditions, which can be an important factor in catalysis. At the same time, a whole set of techniques has been developed for the separation of these soluble polymeric supports from small target molecules. Finally, miscellaneous separation techniques, such as phase-switchable tags for precipitation by chemical modification or magnetic beads, can accelerate the separation of compounds in a parallel format.

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Section: Perfluoro-tagged Reagentsmentioning

confidence: 99%

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Tzschucke

Märkert

Bannwarth

et al. 2002

Angew. Chem. Int. Ed.

339

133

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“…Because any complex with even one polyethylene ligand is insoluble at room temperature, precipitation and recovery of the metal or catalyst are favored even when some low molecular weight species are present. We subsequently verified this in studies with a fluorescent europium carboxylate and used this effect to advantage in asymmetric catalysis and metal sequestration where we were able to deliberately add a low molecular weight ligand without affecting catalyst or metal recovery 28, 39, 40…”

Section: Ethylene Oligomer Supportsmentioning

confidence: 81%

“…Finally, the complete control of solubility of metal complexes through the use of a polymer‐bound ligand suggested yet another application of these materials—sequestration of trace metals 40. In work that is still ongoing, we have been able to show that a soluble polymer ligand can be used to design materials that both sense and sequester a trace metal.…”

Section: Trace Metal Sequestration With Soluble Polymersmentioning

confidence: 99%

Using polymers to control substrate, ligand, or catalyst solubility

Bergbreiter

2001

J. Polym. Sci. A Polym. Chem.

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ABSTRACT:The attributes and design of soluble polymer supports for catalysis and synthesis are discussed. By manipulating polymer structure, polymer supports can be prepared so that the solubility of an attached reagent, substrate, or ligand is affected by heating, cooling, pH, or solvent identity. Supports with such engineered solubility are useful both in organic synthesis and catalysis. They can be used as purification handles in organic synthesis as a way to recover catalysts, as a way to turn reactions on or off, and more generally, as a handle for separa- Keywords:polymer-supported synthesis; solubility; lower critical-solution temperature; biphasic; catalysis David Bergbreiter was born in 1948 in Chicago, IL. Through college, he was the product of public education, matriculating from high school in the Chicago public schools and receiving a B.S. in Chemistry from Michigan State University in 1970. He received his Ph.D. in 1974 from the Massachusetts Institute of Technology (MIT) where he worked under the tutelage of Prof. G. Whitesides. At MIT he was exposed to a variety of intellectual experiences in Whitesides' group, working on projects in polymer chemistry, organometallic chemistry, and organic synthesis. Since 1974, he has been a faculty member of Texas A&M University. In Texas, his research has spanned several areas of chemistry including topics like asymmetric synthesis, catalysis, organometallic chemistry, surface chemistry, and physical organic chemistry. After over 26 years, he considers himself an immigrant Texan because he and his wife Lynne own a few acres of land, have a tiny share of an oil well, and have two "native-Texan" daughters, Sarah and Amy.

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“…In order to demonstrate the application possibilities of the phen‐functionalized polar copolymer, P A was employed for the construction of enhanced metal coordinated 3D architectures …”

Section: Resultsmentioning

confidence: 99%

Phenanthroline—A Versatile Ligand for Advanced Functional Polymeric Materials

Rothfuß

Knöfel

Tzvetkova

et al. 2018

Chemistry A European J

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The controlled incorporation of phenanthroline moieties into polymers is introduced, demonstrating their application as metal-ion complexing ligands for the construction of advanced macromolecular structures. Specifically, two phenanthroline-containing monomers based on acrylate and styrene functionalities, were synthesized. Each monomer was readily copolymerized with either N,N-dimethylacrylamide or styrene via nitroxide-mediated polymerization, resulting in narrowly distributed polar or non-polar copolymers. To demonstrate the versatility of the established polymer systems, the polar polymer was employed for transition metal induced single-chain nanoparticle formation, verified by diffusion-ordered NMR and UV/Vis spectroscopy. Furthermore, the non-polar polymer allows facile incorporation of lanthanide ions, creating luminescent metallo-polymers, in-depth characterized by advanced photophysical experiments and 2D NMR measurements.

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Sequestration of Trace Metals Using Water-Soluble and Fluorous Phase-Soluble Polymers

Cited by 48 publications

References 14 publications

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Using polymers to control substrate, ligand, or catalyst solubility

Phenanthroline—A Versatile Ligand for Advanced Functional Polymeric Materials

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